Arsenio Hall returns to a changed, and much more crowded, late-night TV landscape

Meeting Arsenio Hall at a hotel restaurant in Chicago, several things strike you:

He is extremely polite and instantly likable, good qualities in someone once again asking America to spend an hour each weeknight with him. His Chicago background, while relatively short, was very important: He learned to be a standup comedian here.

And, you learn, he has a lot of famous friends. In the course of a half-hour conversation, the still wiry, now-57-year-old mentioned "Magic" (Johnson), "Quincy" (Jones), and "Jay" (Leno), and still more people by their full names: Stevie Wonder, Alec Baldwin, Billy Bush, Bill Maher, Andrew Dice Clay.

Indeed, ask him about re-entering late-night in an era when there are so many more players in that field than when he left it, in 1994, and he relays what some of those friends have been telling him:

"When a Quincy Jones would say, 'I can't believe that you're not gonna try it again,' I'd always say, 'It's crowded, it's crowded. It's not like it was.' And I always got from people — and maybe it's 'cause I want to believe this — from Quincy Jones to Alec Baldwin, people always said, 'But I still think, "You're not there."' And maybe my taste and personality is different enough to create a 19th late-night show that might find a home."

So Hall will put on the fancy threads — minus those early-1990s shoulder pads — reconvene the "Dog Pound," and once again put himself up for public approval.

Bearing the same name as the show that broke ground during its 1989-94 run, the new "Arsenio Hall Show" will try to win audience away from Jay, Dave, Jon, Stephen, Conan, both Jimmys, Chelsea, etc., or at least to build its own viewership from the hundreds of millions of Americans who don't watch any of them.

That's not a bad bet: No matter how many more names there are in late night than there were two decades ago, Hall, still, will be the only African-American host.

Available in the 50 largest markets and more than 85 percent of the country, the show has a production team including CBS Television Distribution and Hall, and its anchor carrier is Tribune Broadcasting's station group, which means it'll be on WGN-Ch. 9 in Chicago weeknights at 10 p.m. (The Chicago Tribune and Tribune Broadcasting are corporate siblings.)

Hall has done what he can to make the return work. Last year, he got himself cast on Donald Trump's "Celebrity Apprentice," in part to get his name back before the public, and ended up winning the thing.

At the same time, some in the African-American community, reacting to Trump's anti-President Obama politics, were telling him not to do the NBC reality show.

"Let's put it like this," Hall says. "Trump is not as popular in the inner city as Kool-Aid. It was a tough bounce to do that show."

He's guested on "The Tonight Show," "Real Time with Bill Maher" and more, and, more recently, he foamed the runway for the show with a summertime promotional tour, including a Chicago stay at the Trump Hotel, where this conversation — edited for print — took place:

Q: Welcome back to Chicago. How long has it been?

A: It all started here. But the last time I was actually here — I try to do something for Father's Day that's cool every year, and maybe two years ago, me and my son flew in. I wanted him to see the Cubs scorebaord because, you know, he's born in the Jumbotron era and just to see a scoreboard where you hang the number, you know?

Q: So how did it all start?

A: I lived in an apartment on River Road. I wanted to be a famous traveling comic. And I'd met a comic in college, a guy named Franklyn Ajaye, who was in a movie called "Car Wash," who came to Kent State to promote the movie. And he told me the downside to being a stand-up: Everybody just hated the travel.

So the first thing I did when I moved here, I moved within walking distance of O'Hare airport. The irony is, I got my big break right there, too. There was a place called the Hyatt and inside a showroom called the Blue Max, and I got to open for a singer named Nancy Wilson there. The jazz singer. Not rock Nancy (of Heart). It just changed my life. She took me on the road, first of all, and eventually told me I should move to L.A. And I moved there and lived with her manager in his guesthouse.